92254-27-8

Usage

InChI:InChI=1/C14H12O3/c1-17-11-7-8-12(13(9-11)14(15)16)10-5-3-2-4-6-10/h2-9H,1H3,(H,15,16)

Upstream product

• 181268-41-7 methyl 4-methoxy-[1,1'-biphenyl]-2-carboxylate 
• 6312-13-6 3-methyl-4-phenylcyclohex-2-en-1-one 
• 591-50-4 iodobenzene 
• 586-38-9 3-Methoxybenzoic acid 
• 345924-12-1 5-methoxy-2-trifluoromethanesulfonyloxy benzoic acid methyl ester 
• 2612-02-4 5-methoxysalicylic acid 
• 2905-82-0 methyl 5-methoxy-2-hydroxybenzoate 
• 103-79-7 1-phenyl-acetone 
• 22921-68-2 2-bromo-5-methoxy-benzoic acid 
• 35450-36-3 methyl 2-bromo-5-methoxybenzoate 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 77-78-1 dimethyl sulfate 
• 52108-18-6 4-hydroxy-biphenyl-2-carboxylic acid 
• 88187-82-0 3-methyl-4-phenylphenol 

Downstream Products

• 613-37-6 4-methoxylbiphenyl 
• 42523-32-0 8-methoxy-6H-dibenzo[b,d]pyran-6-one 

Relevant academic research and scientific papers

Vitamin Catalysis: Direct, Photocatalytic Synthesis of Benzocoumarins via (-)-Riboflavin-Mediated Electron Transfer

An operationally simple protocol is disclosed to facilitate entry to benzo-3,4-coumarins directly from biaryl carboxylic acids without the need for substrate prefunctionalization. Complementary to classic lactonization strategies, this disconnection relies on the oxidation competence of photoactivated (-)-riboflavin (vitamin B2) to generate the heterocyclic core via photoinduced single electron transfer. Collectively, the inexpensive nature of the catalyst, ease of execution, and absence of external metal additives are a convincing endorsement for the incorporation of simple vitamins in contemporary catalysis.

A versatile approach for the synthesis of para -substituted arenes via palladium-catalyzed C-H functionalization and protodecarboxylation of benzoic acids

While a great number of ortho C-H functionalization reactions have been developed and several breakthroughs have been achieved in meta C-H activation, para C-H functionalization is still in its infancy stage. In this article, a versatile strategy for the synthesis of para-substituted arenes has been developed via a tandem process consisting of palladium-catalyzed C-H functionalization and subsequent copper-catalyzed protodecarboxylation of benzoic acids. Both electron-withdrawing and electron-donating functionalities can be introduced into the para positions of arenes bearing a variety of substituents.

Functional Group Interconversion: Decarbonylative Borylation of Esters for the Synthesis of Organoboronates

A new and efficient nickel-catalyzed decarbonylative borylation reaction of carboxylic acid esters with bis(pinacolato)-diboron has been developed. This transformation allows access to structurally diverse aryl as well as alkenyl and alkyl boronate esters with high reactivity, broad substrate scope, and excellent functional-group tolerance. Further experiments show that this protocol can be carried out on a gram scale and applied to orthogonal synthetic strategies.

Palladium-catalyzed methylation and arylation of sp2 and sp 3 C-H bonds in simple carboxylic acids

The use of preformed sodium carboxylates as substrates led to the first observation of facile Pd-insertions into sp3 β-C-H bonds in simple aliphatic acids. Consequently, Pd-catalyzed methylation and arylation of o-C-H bonds in benzoic acids and β-C-H bonds in aliphatic acids using either a phenylboronate, methylboronic acid, or ArI have been achieved via a C-H activation/C-C coupling sequence. Copyright

Chronobiotic activity of N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]- propanamide. Synthesis and melatonergic pharmacology of fluoren-9-ylethyl amides

Compound 2b demonstrated full agonism at both human MT1 and MT2 receptors and demonstrated chronobiotic activity in both acute and chronic rat models, producing an acute phase advance of 32 min at 1 mg/kg and chronically entraining free-running rats with a mean effective dose of 0.23 mg/kg. This compound was significantly less efficacious than melatonin in constricting human coronary artery. A series of fluoren-9-yl ethyl amides (2) were synthesized and evaluated for human melatonin MT1 and MT 2 receptor binding. N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]propanamide (2b) was selected and evaluated in functional assays measuring intrinsic activity at the human MT1 and MT2 receptors and demonstrated full agonism at both receptors. The chronobiotic properties of 2b were demonstrated in both acute and chronic rat models where 2b produced an acute phase advance of 32 min at 1 mg/kg and chronically entrained free-running rats with a mean effective dose of 0.23 mg/kg. Compound 2b is significantly less efficacious than melatonin in constricting human coronary artery.